Details
Stereochemistry | RACEMIC |
Molecular Formula | C9H13NO |
Molecular Weight | 151.2056 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H](N)[C@H](O)C1=CC=CC=C1
InChI
InChIKey=DLNKOYKMWOXYQA-CBAPKCEASA-N
InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m0/s1
Molecular Formula | C9H13NO |
Molecular Weight | 151.2056 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.sciencedirect.com/science/article/pii/S0099542808601719?via%3Dihubhttps://www.ncbi.nlm.nih.gov/pubmed/8381276 | https://www.google.com/patents/US5260073Curator's Comment: Description was created based on several sources, including
http://www.druginfosys.com/drug.aspx?drugcode=569&type=1 | https://www.drugs.com/dosage/phenylpropanolamine.html | https://www.petcarerx.com/medication-guides/about-the-proin-dosage-for-urinary-incontinence/1086?page=all | https://www.federalregister.gov/documents/2014/02/20/2014-03596/phenylpropanolamine-withdrawal-of-approval-of-13-new-drug-applications-and-7-abbreviated-new-drug
Sources: http://www.sciencedirect.com/science/article/pii/S0099542808601719?via%3Dihubhttps://www.ncbi.nlm.nih.gov/pubmed/8381276 | https://www.google.com/patents/US5260073
Curator's Comment: Description was created based on several sources, including
http://www.druginfosys.com/drug.aspx?drugcode=569&type=1 | https://www.drugs.com/dosage/phenylpropanolamine.html | https://www.petcarerx.com/medication-guides/about-the-proin-dosage-for-urinary-incontinence/1086?page=all | https://www.federalregister.gov/documents/2014/02/20/2014-03596/phenylpropanolamine-withdrawal-of-approval-of-13-new-drug-applications-and-7-abbreviated-new-drug
(+)-Phenylpropanolamine is an enantiomer of propanolamine. The substance has low adrenergic activity and exerts measurable physiological effect only at high doses, which were lethal to experimental animals tested. Phenylpropanolamine belongs to the sympathomimetic amine class of drugs and is structurally related to ephedrine. The effects of phenylpropanolamine are largely the result of alpha-adrenergic agonist activity resulting from both direct stimulation of adrenergic receptors and release of neuronal norepinephrine. Phenylpropanolamine containing products has been withdrawn by FDA due to the association of phenylpropanolamine use with increased risk of hemorrhagic stroke.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2094251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8381276 |
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Target ID: CHEMBL2095203 |
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Target ID: CHEMBL319 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12238918 |
9.8 µM [Ki] | ||
Target ID: CHEMBL315 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12238918 |
280.0 µM [EC50] | ||
Target ID: CHEMBL326 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12238918 |
8.4 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Sources: https://www.google.com/patents/US5260073 |
Primary | Unknown Approved UseUnknown |
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Sources: https://www.google.com/patents/US5260073 |
Primary | Unknown Approved UseUnknown |
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Primary | PHENYLPROPANOLAMINE Approved UsePhenylpropanolamine (HCl) is mainly used as a nasal decongestant. Phenylpropanolamine (HCl) is also used as anorexiant in obesity |
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Primary | PHENYLPROPANOLAMINE Approved UsePhenylpropanolamine (HCl) is mainly used as a nasal decongestant. Phenylpropanolamine (HCl) is also used as anorexiant in obesity |
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Primary | CODAMINE Approved UseUnknown Launch Date9.700992E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
107 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11361053/ |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENYLPROPANOLAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1104 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11361053/ |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENYLPROPANOLAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11361053/ |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENYLPROPANOLAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
225 mg single, oral Overdose Dose: 225 mg Route: oral Route: single Dose: 225 mg Co-administed with:: brompheniramine, p.o(36 mg, single) Sources: Page: p.825 |
healthy, 14 n = 1 Health Status: healthy Age Group: 14 Sex: F Population Size: 1 Sources: Page: p.825 |
Disc. AE: Cardiomyopathy... AEs leading to discontinuation/dose reduction: Cardiomyopathy Sources: Page: p.825 |
25 mg 2 times / day multiple, oral Recommended Dose: 25 mg, 2 times / day Route: oral Route: multiple Dose: 25 mg, 2 times / day Sources: Page: p.100 |
healthy, 25 n = 1 Health Status: healthy Condition: Weight control Age Group: 25 Sex: F Population Size: 1 Sources: Page: p.100 |
Disc. AE: Myocardial infarction... AEs leading to discontinuation/dose reduction: Myocardial infarction Sources: Page: p.100 |
2000 mg single, oral Overdose Dose: 2000 mg Route: oral Route: single Dose: 2000 mg Co-administed with:: caffeine, p.o(8 g, single) Sources: Page: p.52 |
unhealthy, 31 n = 1 Health Status: unhealthy Condition: Schizophrenia Age Group: 31 Sex: F Population Size: 1 Sources: Page: p.52 |
Disc. AE: Vomiting, Hypertension... AEs leading to discontinuation/dose reduction: Vomiting Sources: Page: p.52Hypertension |
150 mg single, oral Recommended Dose: 150 mg Route: oral Route: single Dose: 150 mg Co-administed with:: caffeine, p.o(280 mg, single) Sources: Page: p.510 |
healthy, 56 n = 1 Health Status: healthy Condition: Weight control Age Group: 56 Sex: F Population Size: 1 Sources: Page: p.510 |
Disc. AE: Headache, Vomiting... AEs leading to discontinuation/dose reduction: Headache (severe) Sources: Page: p.510Vomiting Intracranial hemorrhage |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Cardiomyopathy | Disc. AE | 225 mg single, oral Overdose Dose: 225 mg Route: oral Route: single Dose: 225 mg Co-administed with:: brompheniramine, p.o(36 mg, single) Sources: Page: p.825 |
healthy, 14 n = 1 Health Status: healthy Age Group: 14 Sex: F Population Size: 1 Sources: Page: p.825 |
Myocardial infarction | Disc. AE | 25 mg 2 times / day multiple, oral Recommended Dose: 25 mg, 2 times / day Route: oral Route: multiple Dose: 25 mg, 2 times / day Sources: Page: p.100 |
healthy, 25 n = 1 Health Status: healthy Condition: Weight control Age Group: 25 Sex: F Population Size: 1 Sources: Page: p.100 |
Hypertension | Disc. AE | 2000 mg single, oral Overdose Dose: 2000 mg Route: oral Route: single Dose: 2000 mg Co-administed with:: caffeine, p.o(8 g, single) Sources: Page: p.52 |
unhealthy, 31 n = 1 Health Status: unhealthy Condition: Schizophrenia Age Group: 31 Sex: F Population Size: 1 Sources: Page: p.52 |
Vomiting | Disc. AE | 2000 mg single, oral Overdose Dose: 2000 mg Route: oral Route: single Dose: 2000 mg Co-administed with:: caffeine, p.o(8 g, single) Sources: Page: p.52 |
unhealthy, 31 n = 1 Health Status: unhealthy Condition: Schizophrenia Age Group: 31 Sex: F Population Size: 1 Sources: Page: p.52 |
Intracranial hemorrhage | Disc. AE | 150 mg single, oral Recommended Dose: 150 mg Route: oral Route: single Dose: 150 mg Co-administed with:: caffeine, p.o(280 mg, single) Sources: Page: p.510 |
healthy, 56 n = 1 Health Status: healthy Condition: Weight control Age Group: 56 Sex: F Population Size: 1 Sources: Page: p.510 |
Vomiting | Disc. AE | 150 mg single, oral Recommended Dose: 150 mg Route: oral Route: single Dose: 150 mg Co-administed with:: caffeine, p.o(280 mg, single) Sources: Page: p.510 |
healthy, 56 n = 1 Health Status: healthy Condition: Weight control Age Group: 56 Sex: F Population Size: 1 Sources: Page: p.510 |
Headache | severe Disc. AE |
150 mg single, oral Recommended Dose: 150 mg Route: oral Route: single Dose: 150 mg Co-administed with:: caffeine, p.o(280 mg, single) Sources: Page: p.510 |
healthy, 56 n = 1 Health Status: healthy Condition: Weight control Age Group: 56 Sex: F Population Size: 1 Sources: Page: p.510 |
PubMed
Title | Date | PubMed |
---|---|---|
Phenylpropanolamine-associated headache. | 1985 Apr |
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Intracranial hemorrhages due to phenylpropanolamine. | 1985 May-Jun |
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[Cerebral hemorrhage associated with the use of phenylpropanolamine. Clinical cases]. | 1996 Dec |
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The overactive bladder in children: a potential future indication for tolterodine. | 2001 Apr |
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Failure of tolterodine to treat clozapine-induced nocturnal enuresis. | 2001 Jul-Aug |
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Clarification--Drug risk in patients with glaucoma. | 2001 Jun 11 |
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The effect of tolterodine on the pharmacokinetics and pharmacodynamics of a combination oral contraceptive containing ethinyl estradiol and levonorgestrel. | 2001 Nov |
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Pharmacological properties of A-204176, a novel and selective alpha1A adrenergic agonist, in in vitro and in vivo models of urethral function. | 2001 Nov 30 |
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Intense and recurrent déjà vu experiences related to amantadine and phenylpropanolamine in a healthy male. | 2001 Sep |
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Maternal medication use and risks of gastroschisis and small intestinal atresia. | 2002 Jan 1 |
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A possible trend suggesting increased abuse from Coricidin exposures reported to the Texas Poison Network: comparing 1998 to 1999. | 2002 Jun |
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Treatment of overactive bladder: the Antimuscarinic Clinical Effectiveness Trial. | 2002 Oct |
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HPLC determination of phenylpropanolamine in pharmaceutical OTC preparations. | 2002 Oct |
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Adrenergic drugs for urinary incontinence in adults. | 2003 |
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Both alpha1-adrenergic and D(1)-dopaminergic neurotransmissions are involved in phenylpropanolamine-mediated feeding suppression in mice. | 2003 Aug 21 |
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Intracellular signaling pathways for norepinephrine- and endothelin-1-mediated regulation of myocardial cell apoptosis. | 2004 Apr |
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Hidden amphetamines: from smoking cessation to diabetes. | 2004 Feb |
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Fatal pulmonary arterial hypertension associated with phenylpropanolamine exposure. | 2004 Jul |
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Examination of aqueous oxidized cellulose dispersions as a potential drug carrier. I. Preparation and characterization of oxidized cellulose-phenylpropanolamine complexes. | 2004 Oct 8 |
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A validated chiral HPLC method for the enantiomeric separation of tolterodine tartarate. | 2004 Sep 3 |
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Pharmacological management of overactive bladder : a systematic and critical review of published economic evaluations. | 2005 |
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Tolterodine for the treatment of overactive bladder: a review. | 2005 Apr |
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Effects of solifenacin succinate (YM905) on detrusor overactivity in conscious cerebral infarcted rats. | 2005 Apr 4 |
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Antimuscarinic agents exhibit local inhibitory effects on muscarinic receptors in bladder-afferent pathways. | 2005 Feb |
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Should we switch over to tolterodine in every child with non-neurogenic daytime urinary incontinence in whom oxybutynin failed? | 2005 Feb |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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Juvenile pig detrusor: effects of propiverine and three of its metabolites. | 2005 Nov 7 |
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Enantiomeric determination of ephedrines and norephedrines by chiral derivatization gas chromatography-mass spectrometry approaches. | 2005 Oct 15 |
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Nighttime dosing with tolterodine reduces overactive bladder-related nocturnal micturitions in patients with overactive bladder and nocturia. | 2006 Apr |
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[Comment on the STAR study: Comparison of the efficacy and tolerance of solifenacin and tolterodine retard in the treatment of overactive bladder]. | 2006 Jul |
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Tolterodine extended release improves patient-reported outcomes in overactive bladder: results from the IMPACT trial. | 2006 Jun |
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Comparative evaluation of efficacy of use of tamsulosin and/or tolterodine for medical treatment of distal ureteral stones. | 2007 Apr |
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Mixed urinary incontinence: continuing to confound? | 2007 Dec |
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The nonmedical use of prescription ADHD medications: results from a national Internet panel. | 2007 Oct 31 |
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Effect of tolterodine on sleep structure modulated by CYP2D6 genotype. | 2008 Jul |
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How many drugs for LUTS due to BPH are too many? | 2008 Sep |
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Asymmetric conjugate reductions of coumarins. A new route to tolterodine and related coumarin derivatives. | 2009 Dec 3 |
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Keep an eye on the pupil: developing countries under chemical attack. | 2009 Jun |
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Transdermal delivery of tolterodine by O-acylmenthol: In vitro/in vivo correlation. | 2009 Jun 5 |
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Mean arterial pressure: therapeutic goals and pharmacologic support. | 2010 Apr |
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Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
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Transobturator vaginal tape inside out for treatment of urethral sphincter mechanism incompetence: preliminary results in 7 female dogs. | 2010 Dec |
|
Cystoscopic diagnosis and treatment of ectopic ureters in female dogs: 16 cases (2005-2008). | 2010 Jul 15 |
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Syndrome of inappropriate antidiuretic hormone associated with tolterodine therapy. | 2010 May |
Sample Use Guides
Usual Adult Dose for Nasal Congestion 25 mg orally every 4 hours.
-or-
75 mg orally extended release every 12 hours.
Not to exceed 150 mg/day.
Usual Adult Dose for Weight Loss 25 mg orally 3 times a day, one-half hour before meals.
-or-
75 mg orally extended release once a day in the morning.
The use of phenylpropanolamine for weight loss should be limited to 12 weeks.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20179577
Curator's Comment: phenylpropanolamine inhibits platelet aggregation
Unknown
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 23:31:45 UTC 2023
by
admin
on
Wed Jul 05 23:31:45 UTC 2023
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Record UNII |
33RU150WUN
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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WHO-ATC |
R01BA01
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WHO-VATC |
QR01BA51
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WHO-VATC |
QR01BA01
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DEA NO. |
1225
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WHO-VATC |
QG04BX91
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WHO-ATC |
R01BA51
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NCI_THESAURUS |
C87053
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CFR |
21 CFR 1315.13
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CFR |
21 CFR 1314.20
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CFR |
21 CFR 520.1760
Created by
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Code System | Code | Type | Description | ||
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CHEMBL61006
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33RU150WUN
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M8687
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PRIMARY | Merck Index | ||
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PHENYLPROPANOLAMINE
Created by
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C29364
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2149
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4955
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14838-15-4
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33RU150WUN
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8175
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SUB09790MIG
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9920
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100000082264
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8104
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6485
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DB00397
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238-900-2
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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BINDER->LIGAND |
BINDING
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PARENT->PRECURSOR |
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PARENT->PRECURSOR |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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ENANTIOMER -> RACEMATE |
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METABOLIC ENZYME -> INHIBITOR | |||
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SUB_CONCEPT->SUBSTANCE | |||
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ENANTIOMER -> RACEMATE |
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Related Record | Type | Details | ||
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PARENT -> METABOLITE ACTIVE |
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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